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Our top choices for Winter Garden hotels

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center
3.0 star property
Bay Lake
9.4 out of 10, Exceptional, (4,761 reviews)
"Great stay"
United States
La Shaunn
The price is 2.450.364 ₫
2.756.659 ₫ total
includes taxes & fees
3 Jun - 4 Jun
Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
3.5 star property
Bay Lake
9.0 out of 10, Wonderful, (2,228 reviews)
"Amazing place to stay "
United States
Mirian
The price is 2.323.894 ₫
2.614.381 ₫ total
includes taxes & fees
18 May - 19 May
SpringHill Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

Home2 Suites by Hilton Orlando at Flamingo Crossings

Home2 Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
Bay Lake
9.2 out of 10, Wonderful, (5,503 reviews)
"Great stay!"
United States
Pamela
The price is 2.895.118 ₫
3.257.008 ₫ total
includes taxes & fees
25 May - 26 May
Home2 Suites by Hilton Orlando at Flamingo Crossings

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance
3.5 star property
Bay Lake
9.0 out of 10, Wonderful, (1,718 reviews)
"We loved the breakfast buffet"
United States
Florencia
The price is 2.344.972 ₫
2.638.095 ₫ total
includes taxes & fees
31 May - 1 Jun
TownePlace Suites Orlando at FLAMINGO CROSSINGS® Town Center/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance
3.0 star property
Bay Lake
9.6 out of 10, Exceptional, (2,048 reviews)
"Clean hotel with yummy breakfast varieties and great location"
United States
Ramon Noel
The price is 2.898.280 ₫
3.260.564 ₫ total
includes taxes & fees
8 Jun - 9 Jun
Residence Inn by Marriott Orlando Flamingo Crossing/Western Entrance

Home2 Suites By Hilton Winter Garden

Home2 Suites By Hilton Winter Garden
3.0 star property
Winter Garden
9.4 out of 10, Exceptional, (448 reviews)
"Enjoyed my stay "
United States
Nadia
The price is 3.435.252 ₫
3.864.657 ₫ total
includes taxes & fees
21 May - 22 May
Home2 Suites By Hilton Winter Garden

Homewood Suites by Hilton Orlando at Flamingo Crossings

Homewood Suites by Hilton Orlando at Flamingo Crossings
3.0 star property
Bay Lake
9.4 out of 10, Exceptional, (2,420 reviews)
"Excellent breakfast, clean and cozy rooms, beautiful pool with water slide "
Canada
Justin
The price is 3.219.199 ₫
3.621.599 ₫ total
includes taxes & fees
14 Jun - 15 Jun
Homewood Suites by Hilton Orlando at Flamingo Crossings

Orange County National Lodge

Orange County National Lodge
3.0 star property
Horizon West
7.4 out of 10, Good, (261 reviews)
"A GREAT golf vacation experience!!"
United States
David
The price is 3.477.936 ₫
3.912.677 ₫ total
includes taxes & fees
1 Jun - 2 Jun
Orange County National Lodge

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando
4.0 star property
Winter Garden
8.0 out of 10, Very good, (9,852 reviews)
"Beautiful family friendly resort!"
United States
Amber
The price is 4.347.420 ₫
6.343.281 ₫ total
includes taxes & fees
21 May - 22 May
The Grove Resort & Water Park Orlando

Hilton Vacation Club Aqua Sol Orlando West

Hilton Vacation Club Aqua Sol Orlando West
4.0 star property
Winter Garden
8.8 out of 10, Excellent, (3,942 reviews)
"Great stay!"
United States
Katie
The price is 2.634.800 ₫
3.705.320 ₫ total
includes taxes & fees
21 May - 22 May
Hilton Vacation Club Aqua Sol Orlando West

Upstay - Condo Near Disney w Pool-spa-sauna-games

Upstay - Condo Near Disney w Pool-spa-sauna-games
2.0 star property
Winter Garden
The price is 2.369.212 ₫
6.680.306 ₫ total
includes taxes & fees
3 Jun - 4 Jun
Upstay - Condo Near Disney w Pool-spa-sauna-games

Near Disney - Family Condo w Pool, Games, and More

Near Disney - Family Condo w Pool, Games, and More
3.0 star property
Winter Garden
The price is 1.976.100 ₫
6.639.696 ₫ total
includes taxes & fees
18 May - 19 May
Near Disney - Family Condo w Pool, Games, and More

Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is 4.821.684 ₫
13.401.647 ₫ total
includes taxes & fees
15 May - 16 May
Fire Pit & Yard: Updated Winter Garden Home!

Oakland Manor House

Oakland Manor House
3.0 star property
Oakland
The price is 17.099.852 ₫
27.089.037 ₫ total
includes taxes & fees
18 May - 19 May
Oakland Manor House

Upstay Condo Near Disney w Pool & Sauna

Upstay Condo Near Disney w Pool & Sauna
3.0 star property
Winter Garden
The price is 1.949.752 ₫
6.610.055 ₫ total
includes taxes & fees
20 May - 21 May
Upstay Condo Near Disney w Pool & Sauna

Upstay Modern 2BR Condo Near Disney

Upstay Modern 2BR Condo Near Disney
2.0 star property
Winter Garden
Upstay Modern 2BR Condo Near Disney

Upstay Condo w Pool Sauna Sleeps 8

Upstay Condo w Pool Sauna Sleeps 8
2.0 star property
Winter Garden
The price is 2.429.168 ₫
7.370.229 ₫ total
includes taxes & fees
18 May - 19 May
Upstay Condo w Pool Sauna Sleeps 8

Condo With Sauna, Games, Poolnear Disney

Condo With Sauna, Games, Poolnear Disney
3.0 star property
Winter Garden
Condo With Sauna, Games, Poolnear Disney

Rosen Shingle Creek

Rosen Shingle Creek
4.5 star property
Orlando
9.4 out of 10, Exceptional, (4,776 reviews)
"Super nice place to stay at "
United States
Angelica
The price is 3.140.682 ₫
3.533.268 ₫ total
includes taxes & fees
27 May - 28 May
Rosen Shingle Creek

Margaritaville Resort Orlando with H2O Waterpark

Margaritaville Resort Orlando with H2O Waterpark
4.0 star property
Kissimmee
8.8 out of 10, Excellent, (3,593 reviews)
"Clean room and very very nice staff."
United States
Natjaree
The price is 3.884.222 ₫
5.844.031 ₫ total
includes taxes & fees
25 May - 26 May
Margaritaville Resort Orlando with H2O Waterpark
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Where to stay in Winter Garden

Find the best Winter Garden areas for the activities you enjoy most. Learn more about Winter Garden
Learn more about Winter Garden

Downtown Winter Garden

Historic City centre Winter Garden charms visitors with its beautifully preserved early 20th century buildings along brick-lined Plant Street. The restored 1935 Garden Theatre anchors this pedestrian-friendly district where wide pavements invite leisurely exploration. Regular street events and a popular farmers market create a lively atmosphere throughout the week. Cyclists will love accessing the scenic West Orange Trail that runs through city centre. History buffs can explore the Central Florida Railway Museum and Heritage Museum to discover local stories. The area's artisanal shops, farm-to-table restaurants, and outdoor dining spots make this walkable district perfect for a relaxed Florida getaway.

Horizon West

While visiting Horizon West, you might make a stop by sights like Walt Disney World® Resort and Orange County National Golf Club.

Vista del Lago

Vista del Lago offers a peaceful retreat just minutes from Orlando's world-famous attractions. This welcoming Four Corners community features resort-style amenities including sparkling pools and recreation areas. Families appreciate the quiet residential setting after busy theme park days. Wide streets lined with Mediterranean-style holiday homes create a relaxing atmosphere for travellers. Disney's Animal Kingdom and Magic Kingdom are just a short drive away. Most visitors enjoy having kitchen facilities and private spaces while staying close to Orlando's excitement.

Oakland

Oakland charms visitors with its well-preserved historic buildings and small-town atmosphere just outside Orlando's bustling tourist zones. Victorian homes line oak-canopied streets while the city centre area offers antique shops and local cafes. The 128-acre Oakland Nature Preserve provides scenic boardwalks through cypress wetlands. Lake Apopka shoreline offers excellent bird watching with over 200 species. History buffs will appreciate the 1889 Healthy House Museum and railway heritage. Most businesses close early, creating a peaceful evening environment. The West Orange Trail connects cyclists to Winter Garden's wider area.

Killarney

Killarney offers a peaceful retreat from Orlando's tourist bustle while keeping adventure within reach. This family-friendly suburb surrounds you with manicured lawns, palm trees, and quiet residential streets. The nearby West Orange Trail and Lake Apopka provide perfect settings for outdoor recreation. Budget-conscious travellers will appreciate the affordable accommodation and relaxed atmosphere. Take morning strolls along spacious pavements or visit Oakland Nature Preserve just minutes away. A car is essential for exploring Winter Garden's charming city centre and reaching Orlando's famous attractions.

Stay near popular Winter Garden attractions

Learn more about Winter Garden

Stroll the charming brick-lined streets of historic city centre where the Plant Street Market buzzes with local food vendors and craft beer. Pedal along the West Orange Trail that cuts through town, stopping at the Heritage Museum or to catch a show at the Garden Theatre.

ARM53A Historic Downtown Area and Clock of Winter Garden Florida

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Frequently asked questions

What's the weather like in Winter Garden?
The hottest months are usually August and July, with an average temperature of 28°C, while the coldest months are January and February, with an average of 18°C. The rainiest months in Winter Garden are August, July, September and June, with each month seeing an average of 217 mm of rainfall.